Senior Technical Support & Success Manager

Location: Hybrid (Montréal, QC | Toronto, ON | Halifax, NS)

Reports to: Head of Customer Support & Success

Trolley is the payouts platform for the internet economy. Our mission is to unlock the global economic opportunity of the internet by building a truly borderless payouts ecosystem.

Through our platform and API, Trolley enables businesses to pay people anywhere in the world, supporting creators, on-demand workers, and suppliers panies rely on Trolley as mission-critical infrastructure to automate payouts, collect tax and banking information, and reduce fraud and risk, all in one place.

Today, Trolley is the trusted payouts solution for hundreds of businesses, including Canva, Sound Cloud, and Envato. We’ve processed millions of payments globally, helping creators, artists, and suppliers get paid quickly, securely, and with confidence.

As we continue to grow, we’re looking for a customer-focused technical expert who is passionate about building strong client relationships, solving complex challenges, and helping customers realize the full value of the Trolley platform. This role can be based in Montréal, Toronto, or Halifax , working in a hybrid environment alongside our collaborative and globally distributed team.

As a Senior Technical Customer Success Manager, you will play a critical role in delivering an exceptional customer experience throughout the customer lifecycle. You will combine deep technical product knowledge with strong relationship management skills to support customers, drive product adoption, and act as a trusted advisor for some of our most strategic accounts.

Working closely with Product, Engineering, Sales, and Customer Success teams, you’ll resolve complex technical issues, identify opportunities to improve customer outcomes, and advocate for enhancements that strengthen our platform.

This is an ideal opportunity for someone who enjoys balancing technical problem-solving with consultative customer engagement and is passionate about helping customers succeed.

• Deliver world-class customer experiences with professionalism, empathy, and a customer-first mindset.
• Build trusted relationships with customers by understanding their business goals and helping them maximize the value of Trolley’s platform.
• Manage a portfolio of assigned customer accounts, providing proactive guidance, personalized support, and ongoing account management.
• Deliver consultative recommendations that help customers improve workflows and achieve business objectives.
• Handle challenging customer conversations with confidence, influencing positive outcomes while maintaining strong relationships.

• Serve as a subject matter expert across Trolley’s products, including Pay, Tax, Trust, and Sync.
• Troubleshoot complex product, integration, and API-related issues, acting as a Level 2 technical resource before escalating to Product or Engineering.
• Diagnose technical challenges, identify root causes, and provide timely, effective solutions.
• Collaborate closely with Product and Engineering teams to resolve customer issues efficiently while keeping customers informed throughout the process.
• Develop a deep understanding of Trolley’s platform and emerging capabilities to effectively support customers and internal teams.

• Monitor customer adoption and platform usage to identify opportunities for increased engagement and long‑term success.
• Analyze customer data, trends, and usage metrics to proactively recommend improvements and best practices.
• Help customers optimize their use of Trolley’s products through education, onboarding support, and ongoing…